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Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor–Acceptor Cyclopropanes

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posted on 29.05.2013 by Hu Xiong, Hao Xu, Saihu Liao, Zuowei Xie, Yong Tang
A highly diastereo- and enantioselective BOX/Cu­(II)-catalyzed C2,C3-cyclopentannulation of indoles with donor–acceptor cyclopropanes has been developed on the basis of asymmetric formal [3 + 2] cycloaddition of indoles. This reaction provides rapid and facile access to a series of enantioenriched cyclopenta-fused indoline products and can be further extended to the construction of tetracyclic pyrroloindolines. The synthetic potential of the reaction was demonstrated in a four-step synthesis of the core structure of borreverine.

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